Perfume oils containing 3-methyl-1-nonyn-3-ol



=3. Names-l United States Patent O ce PERFUME OILS CONTAINING3-METHYL-1- NONYN-S-OL Thomas F. Wood, Little Falls, N.J., assignor toThe Givaudan Corporation, New York, N.Y., a corporation of New Jersey NoDrawing. Application November 9, 1955 Serial No. 546,005

1 Claim. (Cl. 167--94) This invention relates to perfume-containingcompositions, and more especially to such compositions as cosmeticcreams, detergent soaps, perfume oils and the like, which contain3-methyl-1-nonyn-3-ol.

As is well known, many ingredients used in perfumery have naturalorigins, i.e., they are obtained from a natural source. In many casesthe source is a distant one. As a result, the products obtained fromsuch sources are often characterized by non-uniformity as regards notonly composition but also as regards prices, which fluctuate over wideranges, and availability, which is affected by political upheavals andlocal and general wars. An example of a widely-used perfume ingredientwhich has a natural source is linalool.

An object of this invention is to provide a synthetic substitute for thenaturally-occurring linalool. A further object is to provide replacementfor linalool which has desirable olfactory properties and at the sametime can be made at a relatively inexpensive cost and in ample amounts.Other objects of this invention will be apparent from the followingdescription.

In accordance with my invention I utilize 3-methyl-lnonyn-3-ol as anolfactory ingredient in perfume-contain ing compositions such ascosmetic creams, detergent soaps, perfume oils and the like The termperfume-containing compositions herein is intended to mean perfume oils,cosmetic creams and detergent soap.

The amounts of 3-methyl-1-nonyn3-ol employed difier according to thedesires of the compounder and the nature of the composition. been foundthat, in general, a cosmetic cream having from about 0.01 to about 0.8percent by weight of 3- methyl-'1-nonyn-3-ol on the weight of thefinished cream gives satisfactory results, amounts from about 0.1% toabout 0.3% being especially satisfactory. Detergent soaps having fromabout 0.01 to about 0.5 percent by weight of 3-methyl-l-nonyn-3-ol onthe'weight of the finished bar of soap give desirable results, amountsfrom about 0.1 to about 0.2 percent giving especially desirable results.Perfume oils having from about 1.0 to about 80 percent of3-methyl-l-nonyn-3-ol on the weight formula total are satisfactory,amounts from about 20 to about percent being recommended in general.

The novel perfume ingredient herein-disclosed has been described in thescientific literature. In this connection reference is made to thefollowing citationsfor methods of preparing the S-methyl-l-nonyn-B-ol:Compt. rend., 234,.1557-9 (1952); J.A.C.S., 69, 239-41 (1947); and US.Patent 2,385,547.

The novel ingredient for the purposes of this invention may beincorporated in perfume-containing compositions in the conventionalmanner and hence no special directions are thought to be necessary here.

The compositions containing 3-methyl-1-nonyn-3-ol have imparted to thema light, highly-diffusing floral character without any resultantdiscoloration being caused by the 3-methyl-1-nonyn-3-ol.

For purposes of illustration it has- In order further to clarify myinvention, the following 2,918,412 Patented Dec. 22, 1959 examples aregiven, it being understood that they are for purposes of illustrationand not for purposes of limitation.

Example I 0.2 gram of 3-methyl-l-nonyn-3-ol was incorporated into 20.0grams of white milled toilet soap by weighing the soap and3-methyl-1-nonyn-3-ol, milling them together in a porcelain mortar untilthey are intimately combined, adding to them 2.0 gms. of distilledwater, further milling until the mixture has a homogeneous plasticconsistency and then compressing this mass into a soap cake by means ofa stainless steel tablet-forming die and a hand arbor press.

The soap had a light but fresh floral odor which remained stable formore than 10 months exposed to air and daylight. The color of the soapalso remained the same throughout this 10 month period.

Example II A cosmetic cream was made by melting 12 grams of beeswax in46 grams of mineral oil. Forty grams of a solution of 1 gram of borax in39 grams of water were added slowly to the beeswax-mineral oil melt. Themixture was stirred continuously while being allowed to cool to 50 C.

1.0 gram of 3-methyl1-nonyn-3-ol was added to this cream which wasstirred until the 3-,methyl-1-nonyn-3-ol was intimately combined withit.

The resulting cream was cooled to room temperature and was found to havea stable light floral odor. The cream did not discolor upon standing atroom temperature for 10 months.

Example III A perfume oil having a jasmin character was made by mixingtogether the following ingredients in the amounts given:

Grams 3-methyl-1-nonyn-3-ol 100 Benzyl acetate 200 Amyl cinnamicaldehyde 28 Phenyl ethyl alcohol 100 Hydroxy citronellal 200 Phenoxyethyl iso butyrate p-Cresyl phenyl acetate 28 Indole 1% in benzylbenzoate 22 Phenyl acetaldehyde 50% 10 Cedryl acetate distilled 8Naphthalene 6 N-decanal 10% diethyl phthalate 1 Phenyl propyl aldehyde 2Oil cade 3 Oil peppermint 2 Oil thyme red 3 Oil cedarleaf 3 Solubleresin galbanum 2 Example IV A perfume oil having a honeysuckle characterwas Grams Phenyl acetaldehyde 50% 6 Phenyl acetic acid 4 Oil petitgrainl8 Soluble resin olibanum 6 Geranium bourbon 7 Methyl anthranilate 2Cedrenol 2 Vanillin 2 Oil red thyme 1 Example V A perfume oil having arose character was made by mixing together the following ingredients inthe amounts given:

Example VI A perfume oil having an orange blossom character was made bymixing together the following ingredients in the amounts given:

Grams 3-methy1-1-nonyn-3-ol 200 Nerol 120 Phenyl ethyl alcohol 80Hydroxy citronellal 40 Methyl anthranilate 46 Amyl benzoate 32 Oilbergamot 40 Geranyl formate 20 Benzyl acetate 20 Indole 4 Phenyl aceticacid 4 N-decanal in diethyl phthalate 4 Oil estragon 2 Soluble resinbalsam Peru 3 Methyl acetophenone 2 Oil peppermint 4 Oil Caraway 6 Oilcade 1 Oil citronella-ceylon 1 Example VII A perfume oil having a lilaccharacter was made by mixing together the following ingredients in theamounts given:

Grams Undecalactone 2 Oil spearmint 8 Soluble resin galbanum 1 Oilpatchouly 3 Oil nutmeg 3 Pine needle Siberian 4 Oil cade 5% in alcohol 4Example VIII A perfume oil having the character of coriander oil wasmade by mixing together the following ingredients in the amounts given:

Grams 3-methyl-l-nonyn-3-ol 520 p-Cymene Phellandrene 24 N-decanal 4Borneol technical 8 Benzyl iso amyl ether 8 N-nonanol 6 Furfuryl acetate5 Oil star anise 3 Siberian pine needles 3 Citronella Ceylon 2 Oil cumin2 Coumarin 4 Example IX A perfume oil having the character of cinnamonoil was made by mixing together the following ingredients in the amountsgiven:

Example X A perfume oil having the character of Bois de Rose oil wasmade by mixing together the following ingredients in the amounts given:

' Grams 3-methyl-1-nonyn-3-ol 2600 Terpineol p 200 Myrcene Terpinolene50 Dipentine 50 p-Methyl acetophenone 10 Geraniol 31 Furfural 5 Resinolibanum 15 Oil spike lavender 15 Oil peppermint 25 Oil lemongrassnative 20 Oil rue 27 While I have described my invention in detail inits preferred embodiments, it will be obvious to those skilled in theart that various changes and modifications may be made therein, inparticular in the actual formulations employed, without departing fromthe spirit or scope thereof. I aim in the appended claim to cover allsuch medificatien and ch I claim:

A perfume oil having 3-methy1-1-nonyn-3-ol as an olfactory ingredient.

References Cited in the file of this patent UNITED STATES PATENTS2,385,547 Smith Sept. 25, 1945 2,815,379 Surmantis Dec. 3, 19572,824,896 Surmantis Feb. 25, 1958 Press, Ltd., London, 1949, pp. 13- 20,24, 123, 124, 5 242-249.

Am. Perf., v01. 18, 1924, pp. 621-626.

